With an E Street-inspired saxophone lead and an arrangement straight out of Quincy Jones' playbook, "Cooler" is The Graduating Class leaning into the nostalgia of the 80s. The track features punchy drums, cascading synths, crisp rhythm guitar, and the aforementioned blazing sax line. "Cooler" also marks the Graduating Class' first foray into production, as the band recorded the song themselves in the basement of a shuttered music venue. Lyrically, "Cooler" tells an all-too-universal story about working up the courage to ask someone out; the song's setting is reminiscent of a scene from a John Hughes movie. According to songwriter/producer John Queant: "'Cooler' is about the inner monologue in a person's head as they're trying to ask someone out. I imagined a scene from a cheesy movie, where a total bombshell walks into the club, everyone's jaws hit the floor, and the record skips a beat. The song's narrator is just trying to work up the courage to ask them to dance."